Cesium carbonate → HCID 86761885, compound

HRID 1260568Notes

Reaction equation

HRID 1260568 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[CH2:28][CH:29]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH3:30])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:30][CH:29]([NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[CH3:28])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 144271842-tert-Butoxycarbonylaminopropyl methanesulfonate2×HCID 146926994-[4-(Benzyloxy)phenoxy]phenol

Product 1

HCID 86761885HCID 86761885, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-Benzyloxyphenoxy)phenol (1.948 g, 6.66 mmol), 2-tert-butoxycarbonylaminopropyl methanesulfonate (2.0 g, 6.66 mmol) and cesium carbonate (5.43 g, 16.66 mmol) were stirred in 75 ml of DMF at 80° C. for 3 h. Following addition of 2 g of 2-tert-butoxycarbonylaminopropyl methanesulfonate the reaction mixture was stirred at 80° C. for a further 4 h. The reaction mixture was concentrated in vacuo and the residue is taken up in ethyl acetate and water. The organic phase was separated off, concentrated and the residue was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 837 mg (28%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. customthe residue was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-655edb3832e0497694695e8112c38dc2
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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